


Summer Nights

by Sheiladine



Category: The Simpsons
Genre: F/M
Language: English
Status: In-Progress
Published: 2018-03-27
Updated: 2018-04-25
Packaged: 2019-04-13 14:09:24
Rating: Explicit
Warnings: No Archive Warnings Apply, Rape/Non-Con
Chapters: 7
Words: 11,497
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14114028
Author URL: https://archiveofourown.org/users/Sheiladine/pseuds/Sheiladine
Summary: Lisa returns to Springfield from a year at Harvard, and attends a rowdy party at the park... its a hot summer night and she isn't enjoying herself, until somebody unexpected catches her attention. All characters in serious relationships are depicted as 18+





	1. Summer Night

I do not own The Simpsons or anything related to the franchise. This is purely made for entertainment.

 

Summer Nights

            It was a hot summer night in Springfield, but that didn’t stop one hell of a raging party from taking place at the park at the Springfield water tower. There was a massive amount of liquor, recreational drugs, junk food, loud music, and rowdy patrons; everything a great party needed for bad decisions to be made.

            Lisa Simpson was back in Springfield for the summer from her 2nd year at Yale. She had graduated from Spring Field High School two years early, so she was now coming back as both an18-year-old adult and 2nd year college student. Lisa didn’t know how she ended up at a rowdy party amongst a bunch of familiar rowdy young people…

“And maybe a few old” she thought to herself as she saw Barney drunkenly stumble around the crowd just in sight.

            Lisa reminded herself that she decided to show up only because her brother and a few of her old acquaintances begged her to, but that didn’t stop her from having a bad time as soon as she arrived.

            So far the night decided to subject Lisa to the same old song and dance with Milhouse, who was constantly trying to ask her out, but it only ended up with him running away and crying as usual. There were a few strangers and other drunken acquaintances who tried to ask her to “have a good time”  with equally as bad if not worse finesse.

            Lisa was already tired and miserable even with the night being young and alive, and she soon knew that she needed to find a place to sit down and think, or at least find some time away from all of the shenanigans happening around her. Lisa spotted an empty seat on a bench a bit farther away from all of the commotion t and decided it was a good enough place as ever to hide. Lisa wasn’t paying attention to whoever was sitting on the other side of the bench since it was a bit dark except for the star and moonlight, and all she wanted to do was find a semi-quiet place to sit down.

_…(Earlier)…_

            Jimbo Jones agreed to go to a party with Dolph and Kearney in the park earlier in the day thinking that maybe he could just go to get a little drunk and catch a little tail, but it didn’t really turn out that way. Kearney was at the party before Dolph and Jimbo arrived, and was already shitfaced. A short time after Dolph decided to join him in the tomfuckery and the both of them were already starting to annoy Jimbo. He wasn’t sure why, but he didn’t exactly feel like tipsy flipping with his friends and feel like getting destroyed all night just to wake up in a hungover, blacked-out  stupor (again).

            Shortly, Kearney and Dolph met up with Nelson who was equally in a bad state. Jimbo didn’t even think they noticed that he had finally left. Jimbo took one drink with him and sat on an empty bench and started watching the crowd as they seemingly enjoyed getting themselves trashed and making idiots of themselves. Again, he wasn’t sure why he wasn’t joining them this time. He’d done it plenty of times before. Maybe he just felt burned out right now.  

            Jimbo started contemplating whether he should force himself to drown into a drunken stupor, or if he should just leave when he noticed out of the corner of his eye somebody sit hurriedly next to him. Jimbo didn’t recognize her at first, just that the girl looked horrified and nervous. It took a moment for him to recognize the girl sitting next to him since he had not seen her in quite some time.

“Lisa?” He asked, not quite sure if it was really her or not.

_…(In The Moment)…_

            Lisa looked over at Jimbo nervously, seemingly shocked at hearing her own named be said aloud by someone she, at the time, thought she didn’t know. She nervously looked back at him and stammered,

“Oh! Um… h-hello.”

“So it is you… for a moment there I thought somebody spiked this.” Jimbo said with a smirk holding up his drink.  

“Y-yeah, I was just thinking about leaving…” Lisa laughed nervously. She wondered if it was possible for this night to get any worse.

            She was being cautious. Although Lisa hadn’t spoken to Jimbo in nearly a year, if not more, she wasn’t going to let her guard down around him. She had known him since she was a child, and knew exactly what he was capable of. However, she noticed that he seemed surprisingly sober compared to the rest of the party goers, and she was afraid to admit that she always found him a bit ruggedly attractive… She shook the thought out of her head and looked back at him nervously.

“I was actually thinking about doing the same.” Jimbo sighed and leaned back casually on the bench, looking up at the clear night sky. It was hot night. All of the stars were out, and the moon was just silver sliver of a crescent.

            Lisa started to relax a bit. She thought that maybe by some miraculous chance he wouldn’t try to do anything shady to her, then she mentally scolded herself for being so judgmental, but she was also battling with her frustration over the fact that multiple people had tried to pick her up throughout the night. Lisa supposed it was also her own fault for wearing such a tight, short dress to such an outing. She shook away her thoughts again for a moment and looked back at Jimbo. He was surprisingly not paying any attention to her, or the party. He was just looking up at the sky. She decided to do the same. Lisa thought that it was also surprising that Jimbo, of all people, wouldn’t be interested in getting drunk, high or causing mayhem. Hell, her brother was definitely causing trouble here. Lisa sighed and just looked at the stars.  

“They’re pretty…” Lisa mumbled.

            Jimbo looked over at her curiously and she quickly turned red as she realized that she was thinking aloud.       

“I mean… New Haven is such a big city you can’t see the stars at night as well as you can in Springfield.” Lisa quickly explained.

            Jimbo didn’t say anything for a bit and just looked back up at the stars. Lisa continued to blush, hoping that she didn’t sound like a loser, but then she wondered why she even cared. It was Jimbo, he definitely thought she was a loser.  

“They’re just stars.” He finally commented uncaringly. Lisa looked back at him in slight annoyance and moved over slightly closer to him.

“You only say that because you can see them every day.” Lisa replied hotly.

            Jimbo looked at her with a smug look on his face. He thought it was cute seeing her get angry over something so small.

“Cute? What am I thinking?” He thought to himself, annoyed that he would dare think such a thing about Lisa Simpson.

            Jimbo blushed slightly from the thought and quickly averted his gaze away from her and back up at the sky.

            Lisa didn’t know why, but him ignoring he was starting to stir her up a bit.

“You haven’t changed much.” Jimbo commented, still averting his gaze from hers.

“And neither have you.” Lisa said in defense, but that was a lie. She expected him to be a real sleazebag to her by now. No… maybe she wanted him to be? “Lisa, stop about things like that.” She quietly scolded herself, blushing. She hoped it was too dark for him to see.

            Jimbo finished the rest of his drink and threw the plastic cup behind him and pleasingly noted Lisa’s annoyed expression.

“You can’t just do that!” Lisa contested. “There’s trashcan right over there” She pointed frustratingly.

“Well, I just did.” Jimbo smirked.

            The two locked eyes for just a moment too long and the two of them blushed in unison and quickly looked away. Jimbo started to get up and leave, but as soon as he did he felt her tug on his wrist. He looked back at her curiously, and honestly a bit surprised. This was a bold move for her. At this angle he could see her clearly blushing red.

             As Lisa sat there holding his wrist she silently panicked. She didn’t have any sort of explanation for her actions. She slowly let go of his wrist and looked away.  

“What?” He asked slightly annoyed. “She couldn’t be mad over a stupid cup.” He thought to himself, but this was Lisa Simpson after all.

            Lisa felt a hot sensation in her stomach, and she thought this is truly what people meant when they referred to butterflies in their stomachs. Her face still flushed hot with embarrassment. She forced herself to look back at him. Jimbo had an idea that he thought he knew what was up with her now, but felt like he couldn’t know for sure. He sat back down next to her and brought his face close to hers in what he supposed was an effort to ‘test out the waters’. To Jimbo’s surprise Lisa was the one who confirmed his thoughts by closing the gap in between them by kissing him. Jimbo returned her kiss without a second thought. Lisa moved her hand onto his thigh.

            When their lips parted Lisa took her hand off of him and looked away in utter embarrassment due to her brash actions. She started to feel even more embarrassed by how her whole body felt, especially how she ached for him between her legs.

“I-I’m sorry, I-I didn’t mean t-“ She didn’t get to finish her sentence. Jimbo turned her face back toward his and started to kiss her again, their tongues intertwining. Lisa leaned back into him, more comfortable than the first time. She still couldn’t believe what she was doing, but she didn’t want to stop. When their lips finally parted she couldn’t help but to continue to look at him with a mixture of longing and embarrassment.

“Lisa, do you want to go somewhere more private?” Jimbo asked. He was hoping she would say yes, but didn’t think that she would by the way she reacted from just a kiss. He wouldn’t force her though, and decided he was going home either way. Whether it was with her or by himself he had to get his rocks off soon because of her.

            Lisa paused momentarily, but continued to look at him and nodded. Jimbo had a hard time keeping the dumbstruck look off of his face. He never thought in a million years that she would ever say yes. The two of them got up and went to his car. He was glad he didn’t have more than that one watered down drink.

…(A Little Later)…

            They both supposed that their nerves got the best of them. Neither said anything or looked at each other the entire ride to Jimbo’s house. Both were nervous, though neither would admit it. 

Jimbo lived alone. His mother had a fatal accident while out ‘selling herself’, and his sister moved out shortly after, leaving the house to him. Jimbo led Lisa up to the front door of his house and opened the door. Again, he continued to surprise her. Lisa didn’t expect his house to be clean. “Actually, it barely looks lived in.” She thought to herself curiously. She followed Jimbo to his room, which looked slightly more lived in, but was still lacking the clutter that she assumed he would likely be living in. She scolded herself again for being so judgemental. 

            Jimbo took off his shoes, lied back onto his bed and beckoned her over. Lisa kicked off her sandals and joined him where they continued their make out session from the party in the park.

            Jimbo was trying to be careful with her and he knew that she was unlike any other girl he had been with. He let her make the next move in fear of advancing too fast onto her. He didn’t want her to become overwhelmed and leave. He could also tell that she was very unexperienced. But Lisa, unbeknownst to Jimbo, had no intentions of being overwhelmed and leaving. She just didn’t want to come off as easy, and was hoping that she successfully showed that she was quite the opposite… she knew he had been with a lot of other girls and he didn’t want him to think that she was exactly that, just another girl. Lisa had dated quite a bit, but never went past kissing and dinner dates. This was the closest thing to sex that she had ever done, and hoped he could tell from her actions that she wasn’t experienced at all.

            Although Lisa was unexperienced with many things (and a virgin), she wasn’t sure if she could be satisfied with just kissing and rubbing up against him. Even though she had never had sex, she couldn’t help the desire in between her legs. In her earlier years she never would’ve thought her first time would be with James “Jimbo” Jones, the exact opposite of her in nearly every way, but here she was, practically begging for him. “I’ll chalk it up to those stupid birth control pills I started taking a month ago messing with my hormones.” Lisa thought to herself, annoyed. She started taking them to be ‘extra safe’ while living in the city where anything could happen.

            Something that just crossed Jimbo’s mind was that, even if she did want to have sex, he didn’t have any condoms on him, and Lisa definitely did not strike him as the type of girl to carry any on her. Just his luck, he supposed. He didn’t think she would go that far anyway since she was such a nicely-mannered, timid girl.

            Lisa stuck her hands up his shirt and felt his bare skin against her hands. Jimbo just threw his shirt off since he got the message that she wanted to feel his body against hers. He definitely couldn’t stop his erection from growing from her rubbing up against him. He knew she must’ve noticed by now too, but was just too polite to say anything.

Lisa did notice his erection through his pants and it drove her sexual cravings into overdrive. Her body felt very hot. She decided to slip off her jean jacket and her tight dress. Jimbo watched her intently as she took her clothes off, admiring every inch of her bod. He wanted to take her bra and panties off and look at (and feel) the rest of her body, but he controlled himself. Instead he took his pants off and left himself in his boxers and decided to see how she would advance. He kept reminding himself that she was probably going to leave him hard and yearning for more, and not to get his hopes up.

            The two proceeded to wrap their arms around each other and make out on the bed. Lisa was grinding her hips against his erection. She was very wet and it was showing through her panties. She hoped Jimbo didn’t notice since it embarrassed her to be that visually aroused by him, but she desired more than what was currently happening.

            Lisa hesitantly made the decision to unclip her bra and remove it. Jimbo eyed her hungrily. Lisa moved his hands to her breasts and he eagerly obliged. Lisa let out a very quiet moan of pleasure. Jimbo decided to make a bold move and moved his mouth to one of her breasts and sucked on one of her nipples. She gasped in pleasure and couldn’t help herself but to slide one of her hands into his boxers and grab his cock. Lisa noted that he was very big as she stroked him. He stopped sucking her and gasped at her touch.

“Can we… do it?” Lisa asked breathily.

            Jimbo mentally groaned.

“I don’t have any condoms.” He said defeatedly.

“I’m on birth control… so it’s fine… I don’t know why I did it though. I have never… had… sex…”

            Jimbo’s mind was blown; he wasn’t going to question her decision to be on birth control. It did concern him that she was a virgin, but he wasn’t exactly surprised. He watched as Lisa slide her panties off and he looked at her hungrily. She started to tug at his boxers and he hurriedly took them off. She couldn’t stop looking at his cock once he was completely undressed. She knew he was big when she felt him, but it was a different feeling looking at it. She wanted him desperately. She lied on her back and spread her legs, grabbing him toward her. He was pleasantly surprised. He started kissing her again whilst on top of her.  

            He guided his cock right above her wet opening, and rubbed his member against her clitoris. Lisa whimpered and moaned more audibly and she wrapped her hands around his back. She wanted him inside of her. She knew it would hurt, but she didn’t care, she longed for him to be inside of her. Jimbo put the tip of himself inside of her and she tensed slightly. Lisa felt as he slid into her and she momentarily felt a quick, sharp pain as her hymen tore and she let out a slight whimper of pain. She whimpered as he inserted his entire length into her, he tried to make the pain a quick process instead of a slow one. Lisa was tensing around his cock and was so tight he thought he would almost burst right then and there, especially since he could feel everything, including that unnerving moment when he tore her. He never fucked a virgin, especially not one without a condom, so feeling her tear was a bit disconcerting.  When Lisa started to relax relaxed he started to gently thrust into her more. Moans of pain quickly turned into moans of pleasure.

“J-James, y-yes!” She stammered out loudly, in pleasure.

            Jimbo blushed at her calling him ‘James’, but he was fine with it as long as it was _her_ calling him that. He really wasn’t used to it, but Lisa saying his name in any way drove him crazy. He could feel everything, and knew that he couldn’t hold on much longer. It turned out he didn’t have to, since she was easily (and thankfully) was able to have an orgasm. Lisa shuddered against him in ecstacy and shortly after he released into her. He let out a slight moan as his hot semen spilled into her. Lisa held onto him tight feeling the warm, satisfying sensation of him filling her up. The sensation was maddeningly satisfying as she felt him start to relax on top of her. She wondered if it was like this for every girl he was with, and if he had the same reaction with all of them. Her thoughts were interrupted by him giving her a kiss then rolling next to her. He held her hand and she cuddled into him, deciding to keep those thoughts for a later time.

 


	2. Best Friend

**Notes for the Chapter:**

> Oh no, I decided to add more. For some reason I felt like adding to this story.
> 
> Probably just my addiction to Jimsa and Dolsa.

**Best Friend**

            Shauna sauntered around the party searching for Jimbo. She wanted to have some fun and all of her other options were far too hammered for her to have any sort of good time with. Whiskey dick wasn’t fun. Shauna couldn’t find Jimbo anywhere she looked decided to ask his two bozo friends.  Bart Simpson just also happened to be hanging out with the two when she arrived.

“Hey you two, have you seen Jimbo around have you?” Shauna asked, annoyed that she had to search so hard, or even at all for that matter. Jimbo  should be the one running to her.

“I think I saw him leave with that Simpson girl.” Kearney drunkenly belched. Shortly after Bart quickly turned toward him and yelled,

“What?! Why didn’t you say something earlier?!”

            Dolph looked over at the two groggily before asking,

“Huh, what? Really?”  This weird revelation was starting to make him come out of his drunken stupor. Shauna looked over at Kearney disbelievingly.

“How drunk are you? Oh, never mind. We should go to his house and find out. I wanna see if it’s true or not. Either way, this place is just full of deadbeats.”

            Dolph watched as Kearney stumbled away with Shuana and Bart, hesitantly following the three. He quickly dug his phone out of his pocket and checked it. Four missed calls and three text messages.

“Oh, hell.” Dolph mumbled under his breath. He completely forgot that she was coming back for the summer, and it never crossed his mind that she would show up to a place like this, therefore he didn’t bother to check his phone.  

“Hello, hello old friend. I’m back in Springfield for the summer. Maybe we could catch up and maybe play a round of V&V together later. J”

“Hello there, I was wondering if you were going to that party tonight in the park… I was thinking you might be going since it is more your type of thing and all…”

“This place is a disaster. I was hoping to run into you, but I’m sure you’re just busy… J”

            Dolph frowned as he looked through the messages on his phone. He tried calling her quickly, but it went straight to voicemail. He dreaded to think that what Kearney said he saw was actually true. It couldn’t be right? How could she fall for a guy like Jimbo? _Ever_? It must’ve been a mistake.

_…_

“What in the hell is this?” Shauna jeered with a hint of disgust at the sight of Lisa and Jimbo snuggling up to one another in bed.  

“I told you.” Kearney replied nonchalantly.

            Jimbo and Lisa slowly grimaced awake at the sound of voices, but Lisa snapped into her senses first and gasped as she quickly pulled the bedsheets over her head, completely covering her.

“Nice, man.  That one’s a catch.” Dolph commented with a forced smirk, eyeing her even though she was completely covered by the bedsheets. He had a bit of a pained look in his eyes, but nobody could really tell with all of the commotion.

“What the… Get the hell out!” Jimbo snapped at the four.

“I was just about to say the same to you!” Bart yelled.

“But this is my house!” Jimbo shouted momentarily confused.

Lisa continued to hide under the covers, too embarrassed to look at or say anything to anyone.

“I was hoping this wasn’t true since I really needed an itch scratched, but whatever. Maybe later. I just wanted to see if it was true. At least it’s funny.” Shauna scoffed. She brushed by Dolph alluringly. “But if _you_ want to see me later… you have my number.” She then walked out the door, winking at him before she left. Dolph only momentarily looked at her before averting his attention to the disaster right in front of him.  

            _Typical_. Lisa thought listening to the exchange between the two. She then thought that was probably the reason why he didn’t’ return any of her messages earlier. _It didn’t matter anyway._ She thought once again, until her thoughts were once again interrupted.

“Get away from my sister, you asshat!” Bart shouted.

“You get out of my house, jackass!” Jimbo retorted.

“Maybe you should lock your doors if you don’t want people coming in.” Kearney stated stoically.

“Get out!” Lisa yelled from under the covers.

“But-“ Bart started to say until Jimbo interrupted.

“You heard her.”

 “Fine man, calm down. We’ll be in your living room.” Dolph smirked as he led Bart and Kearney away from the room, looking back at Lisa, who was still hiding under the sheets, venomously as he walked out. They shut the door as they left.  

“They’re gone… well, not in here anymore.” Jimbo said hesitantly to Lisa.

            Lisa slowly lifted her head out of the covers and looked at the clock on the bedside stand. It was 2:30AM. She looked at Jimbo, then looked away in a quiet sadness, with a tinge of embarrassment.

“I’ll kick them out… I just need to get dressed.” He commented quickly.

“O…kay.” Lisa mumbled hesitantly, but she was very grateful.

…

            Once Jimbo was dressed he went out into his living room to deal with his currently unwanted ‘friends’.

“Where’s Lisa? She’s coming back home now!” Bart snapped and Jimbo.

“Uh, no. She doesn’t want to go back with you, she wants to stay here.” Jimbo said tired and annoyed.

“Yeah, like I’m supposed to believe that.” Bart jabbed back.

“Wow, Jimbo. You never let women stay the night with you. She must be _really_ _good_.” Dolph said with another forced smirk, but the look that he gave Jimbo said everything about how jealous he really was, but Jimbo didn’t take any notice. Bart gave Dolph an angry glare for the jibe, which was funny since he felt as if he were probably just as angry…

“The three of you just get out already.” Jimbo sighed defeatedly.

            Kearney, to Jimbo’s relief, dragged a protesting Bart out the door, which just left Dolph sitting on the couch.

“That includes you.” Jimbo scowled at Dolph.

“That’s no way to treat your best friend.” Dolph said mockingly, continuing to force a faked smirk.  

            Jimbo stared back at him slightly dumfounded at how he was acting, thinking that he was probably just poking fun at him for sleeping with Lisa Simpson of all people. He was about to come up with a retort when Lisa slinked out into the living roo, only wearing one of jimbo’s T-Shirts. It was long enough to cover all the parts that mattered. Jimbo turned toward her suddenly.

“Uh, sorry Lisa, I got the other two to leave, I just haven’t been able to deal with this one-“

“He didn’t drug you or anything, did he?” Dolph looked over at her with an automatic change of tone from cynical to serious. That floored Jimbo.

“Uh, what? Ah-no!” Lisa protested then looked down embarrassed. Fidgeting with the bottom of the shirt she was wearing.  

“Good, good… Just makin’ sure, you know… Sorry that I didn’t respond  earlier…I was tied up.“ Dolph got up and walked over to her. Jimbo eyed him suspiciously. The way he was talking to her as if he knew her better than he did inexplicitly got on his nerves.

“Hmm? Oh! That, yeah, I just assumed you were busy, so it’s fine…” She smiled hesitantly back with a friendly demeanor, blushing a bit. _So he was just busy…_ She thought reluctantly.

“I just… wanted to make sure you’re okay.” Dolph blushed a bit before hugging her.

            Jimbo’s mouth was agape. He wasn’t sure what shocked him more, that Dolph got up and hugged her right in front of him or, wait, she _was hugging him back? What the fuck?_ Was he missing something?

            Dolph then walked past Jimbo to leave his house. Jimbo noticed him force one last faked smile and glare at him with a special kind of hatred as he left. He wondered if it was alright to ask her about him or not… or even if he should try and ask him about her later.

“Can we go back to bed? I’m beat.” Lisa said with a slight smile. Jimbo agreed and took her back to his bed. He repressed the reemerging urge to fuck her brains out. He supposed it was just a psychological response to his friend being somewhat close to her, but it wasn’t like Jibo was really that close to her himself. Could he have done the same thing prior to this encounter with her? He assumed not. When they lied back in bed she cuddled into him and he pleasantly embraced her, but hoped his now rekindled erection wasn’t bothering her. This night had been awkward enough…


	3. I Nearly Forgot

**I Nearly Forgot**

            When Lisa woke up Jimbo still had a stiffy. Also, he didn’t sleep well after that encounter with Dolph, awkwardly paired by the everlasting erection Lisa was causing him. Luckily when Lisa woke up she was more than happy to help him with his problem…

…

 “Uh, about last night…” Jimbo mumbled. Both him and Lisa were at the kitchen table. Since she was vegetarian all he had was oranges and grapefruit to give her, but she didn’t seem to care much.

            Lisa froze as she bit into her orange slice when she heard him say those words, having even more thoughts racing through her head. _Oh no, is this the part where he’s going to tell me, yeah, it was great, but let’s keep this a one-time thing okay?_ Lisa hoped not. She became tense, swallowed with some difficult and replied hesitantly,

“Y-yes?”

“You’re not upset, are you?” He asked her, concerned and a bit worried.

            This question took her aback. She wasn’t expecting it.

“What? No, of course not! Why…?”

“You know, Shauna, Kearney… your brother…. Dolph… seeing you, with me.”

“I… I don’t think I mind all that much… do you?”

            She would have to do a lot of explaining to her brother, but she really didn’t care what anybody else thought about her in regard to who she was sleeping with. Springfield was just a small, nobody town…

“Nah, I can handle your brother and Dolph…is…” Jimbo looked away nervously not knowing how to approach the subject with her without seeming jealous or possessive. She was the one thing he wasn’t willing to share with him.

“Huh? Dolph?” Lisa thought for a moment. “Oh!” She quickly realized that he didn’t know that she and Dolph knew each other from years of playing Vikings and Vampires with him, Martin and Milhouse in her basement. He baasically became their babysitter once he was old enough since he was 6-7 years her senior, but nobody really admitted it, though it was convenient. Oh gods, that sounded weird just thinking about it. Dolph probably didn’t want him mentioning that to any of his friends though. She didn’t really want to admit either that she still actively participated in that role playing game lest she sink herself into a deeper pit of geekdom.

“What?” Jimbo asked since she was just smiling nervously.

“Oh, uh… We know each other from a thing some other people and I used to do in my basement back since I was 8 and-“

            The creeped out look on Jimbos face said it all.

“D’oh.” Lisa grimaced, she totally didn’t mean it to sound that bad, but she didn’t’ really want to say what she was doing with him either.

“It’s not as bad as it sounds, I swear. I just… promised I wouldn’t say anything about it, it’s kind of embarrassing.” Lisa grinned nervously.

“Uh… okay. I’ll probably just try and get him to tell me later then, since that really sounds… weird.” Jimbo said, still trying to figure out what in the hell she could be talking about.

            Lisa laughed nervously “Good luck with that, aha-ha…”

            Jimbo leaned over to her and kissed her. It surprised her a little since it was unexpected.

“Well, as long as he’s not into you I guess there won’t be a problem.”

“What? _Dolph_ into _me_? That would be the day.” Lisa laughed.

            But Jimbo wasn’t so sure about that.

…

            Dolph scowled at his sealing as he was lying in bed.

“All these years of lookin’ out for you and this is how it turns out.” He growled. He remembered when he used to spin her on the merry-go-round when she was sad when they were younger.

_“Zine beh-sechel!” He cursed. He also remembered times when he and Jimbo used to torment her when they were younger._

 “It didn’t have to be me, but why him?”

“I just wanted to make sure you’re okay.”

“I j just wanted to tell you I care about you.”

“I just wanted to let you know that I kind of sort of like you okay?”

“I just wanted to let you know that you’re making a big mistake choosing Jimbo, over me since I’ve looked out for you since we were kids okay?”

“Ugh.” Dolph groaned and turned over on his bed, facing the wall. His room was dark since his lights were off and his blinds were down. It was fitting for his mood anyway.

“You came back. You’re old enough now. I can finally get a shot with you now and… what the hell does he have that I don’t?”  

…

            Later that day Dolph decided to stop moping and go outside. He went to spots around Springfield that he knew _she_ frequented in hopes of bumping into her. He didn’t feel bold enough to call or message her, but decided if he saw her in person he’d work up the courage to confront her. One spot he tried was a favorite reading spot of hers in a local park. Unsurprisingly found her there, happily reading, and thankfully alone.  

“L-Lisa, hey.” He stammered before sitting next to her.

“Oh, hello Dolph.” She said happily.

“H-how have you been?” He asked nervously, hoping she didn’t see through his nervous smile.

“Okay, it’s strange being back here…” She trailed off in thought.

“So, you and Jimbo, are you two…?” Dolph said getting straight to the point.

            Lisa sat up straight and closed her book, a nervous reflex.

“Are we…?” She glanced over at Dolph nervously.

“Ya know, a thing…” He couldn’t stop himself from blushing. He knew she must’ve noticed now. _Idiot_ , he chided himself.  

“Oh, I don’t know… I haven’t really talked to him about…. _that_ … and I’m only back for the summer, so it would be long distance and I don’t know if he’d mind that or not…”

“For someone like you he shouldn’t mind…” Dolph looked away from her in embarrassment.

            Lisa looked at him curiously. _Was he hitting on me?_ She thought to herself and blushed _. No, it couldn’t be. He would never be into… that would just be preposterous._ A flashback to her kissing him on the cheek once when they were younger occurred. Why did she think of that? She shook that picture out of her head.

“If only I were older…” She whispered, nearly inaudibly to herself.

“What?” Dolph asked hesitantly.

“Oh, nothing!” She quickly replied.  “You know, Jimbo asked about… the basement.”

“Don’t make it sound so weird.” Dolph protested and Lisa giggled.

“He’ll probably ask you next. I didn’t say what we did…” Lisa said, trying to stifle her laughter.

“Now you’re making it sound like something dirty. I swear you better not have said anything to make it sound like-“

“Yes, something dirty with Milhouse, Martin and I” Lisa giggled and Dolph looked at her now beat red.

“That’s not funny.” Dolph protested. “Ugh, I’ll probably just have to tell him now. Lame.” Dolph groaned.

“We could probably all do it again for old time’s sake.” Lisa replied, still girlishly giggling.

“Stop saying it like that!” Dolph replied annoyed ,and still red from embarrassment.  

“It’s only dirty if your mind’s that way.” Lisa giggled,

“Well, you were thinking the same thing, so I wonder what that says about you.” He smiled at her.

 _“That’s a catch.”_ Echoed in her ears from that night. _Was that just a front for his friends or?..._

“Lisa, I really have to say something…”

            Lisa snapped back into reality at hearing his voice.

“You can tell me anything, you know that…” She said solemnly.

“Well, now knowing you told Jimbo about the basement I’m not sure about that…” He said half-jokingly.

            Lisa started giggling again,

“Hey it’s hard to be serious if you bring that up again.”

            Dolph loved her laugh and her smile. He couldn’t help it. He leaned in closer to her and kissed her.

            Lisa didn’t pull back, but she didn’t exactly return either. She sat there astonished and let it happen. _So he was interested in her…_ Her heart dropped into her stomach and she felt woozy at this revelation. _But what about Jimbo?_ She liked him and he took her… Dolph pulled away from her.

“I… care about you… a lot.” Dolph murmured.

            Lisa still couldn’t say anything, likely from the shock.

“Let me prove it to you.” He added


	4. Lovesick

**Lovesick**

 

 “Woah, did you break up with Jimbo already?” Kearney asked Lisa  curiously.

            Lisa looked over at him terrified for a brief moment until Dolph interrupted,

“You don’t have to answer that, Lisa.” Dolph snapped at Kearney with annoyance, taking Lisa by the hand as he led her to his room.

“Sheesh, just asking a question.” Kearney said. _I gotta ask Jimbo about this._ Kearney thought to himself eagerly and he got out his phone to text Jimbo.

_“Yo, what did you do to make Lisa dump your ass already?”_

…

            Once the door shut behind the two, Dolph and Lisa quietly stared at each other nervously before looking away in embarrassment. Dolph went over to his bed and sat on it and Lisa shortly decided sit next to him.

            “So… is there anything you would like to talk ab-“ Lisa was cut off by Dolph pushing her over on the bed so that he was on top of her, and started kissing her.  Lisa kissed him back passionately, and wrapped her arms around him. She hated to admit it, but she wanted this, and for quite a while. She had wanted to kiss him since she was 8, so quite a while was about the past ten years…

“Lisa I… love you… so much..,” Dolph gasped between kisses. Lisa’s face turned red from the flattery. She honestly had no idea he was this interested in her…

…

 _“Uh, nothing. Why the hell do you wanna know?”_ Jimbo replied via message to Kearney.

_“Uhh, well, I think Dolph may be layin’ it to her right now?”_

_“What the fuck? Are you sure? You can’t be serious right now..”_

_“Well, I’m pretty positive since they’re obviously doing something in his room…”_

            Jimbo looked down at his phone in shock. _There was no way…_ He thought to himself. They hadn’t really talked about anything after she left but his house, but he hoped that she would’ve assumed… He had to go over there right away and fix this mess. _That fucking bastard did have the hots for her._ He thought to himself angrily.

…

            Both Lisa and Dolph had stripped off each other’s clothes off down to their underwear at this point and were continuing to make out and feel up one another. Lisa immediately noticed that she felt very different with Dolph than she did with Jimbo. She felt more of an emotional connection than a physical one to Dolph, and she didn’t know how to exactly interpret that. She really wanted to ravage Jimbo due to the unexplainable physical attraction she had to him, but with Dolph she kind of just wanted to lie there in his arms and continue to be affectionate toward him since he was more familiar…        

            Lisa shivered in pleasure as he delicately traced a finger down her body and he eventually started kissing all the places he touched starting with the nape of her neck, slowly going down… She squirmed a bit in embarrassment as he reached just below her bellybutton. He stopped and let out a slight laugh at her reaction before he brought himself back up to her face and kissed her lips again.

            “You’re so beautiful…” Dolph murmured. Lisa blushed again, but looked away and couldn’t help herself from saying,

            “Then why didn’t you answer any of my calls that day…”

            Dolph grimaced. Lisa wouldn’t look at him even though he was right on top of her.

            “So you’re saying that you only slept with my best friend because I didn’t get back to you in time?” Dolph sneered.

            This time Lisa grimaced. She still couldn’t look at him.

            “You’ve got a lot of nerve to say it’s all my fault. I know you called. I got them all.” He voiced, becoming annoyed with her. Lisa felt his grip tighten on her slightly.

 _“_ I wanted you to be my first, but I didn’t think you were interested…and I guess Jimbo was just there at the right place and time…” Lisa tried to justify. She looked as if she were about to cry.

            “ _What_?” Dolph questioned, it took him a moment to process what she had just revealed. Lisa saw the shock in his eyes. She realized he probably didn’t know she was a virgin before she slept with Jimbo. She even had to tell Jimbo before they did it… She had to look away again. This was another thing she didn’t think she could adequately explain.

“So you didn’t just sleep with him, you lost your virginity to him too?!” Dolph exclaimed, stunned and staggered. He couldn’t comprehend how she could’ve had such a lapse in judgement. He had a hard time believing she _wasn’t_ drunk that night. For some reason he would’ve rather heard that she lost it to some random college student than to Jimbo.  

            Lisa couldn’t stand the disbelief and hurt in his eyes. She thought she was definitely going to cry until he buried his head into her chest and started kissing her again. When he did this he made her whole body shiver.

            Dolph skillfully unhooked her bra and slid off her panties. He admired her naked body lying right in front of him for a while. She burned red as he brushed one of his fingers over one of her nipples, it becoming erect in response. She let out a quiet squeak when he took her legs and spread them so that he was positioned in between them. He was still wearing boxers at this point, but wanted to stop and admire her momentarily. He audibly sighed as he slid down his boxers and positioned himself to enter her. Lisa pondered if it was a sigh of disappointment or not due to her already being...’taken’. She felt as though he must’ve thought of her as used goods due to sleeping with Jimbo. Her thoughts were interrupted once he entered her and started sliding in and out of her with ease. She noticed he wasn’t as big as Jimbo was, but it still felt really good, less painful. She embraced him by wrapping her arms and her legs around him, moaning in pleasure as he continued to thrust into her.

…

            Jimbo entered Kearney and Dolph’s apartment loudly, and abruptly, surprising Kearney to say the least.

“Oh, hey man” Kearney said. He had the television up louder than he normally would, and it was easy to tell why. Jimbo could slightly hear Lisa’s moans in the background.

“Son of a bitch…” Jimbo scowled.

“Oh, yeah. Guess she moves on quickly, huh?” Kearney commented with a shrug.

“She never broke up with me in the first place. That fucking prick.” Jimbo said between clenched teeth.

“Uh, oh… Shit.” Kearney replied, slightly worried by the state of anger his friend was currently in. It was no problem seeing him mad at other people, but seeing him that pissed at Dolph was another thing. If they weren’t fucking some girl they were inseparable. _Maybe not even then…_ Kearney shook that thought from his head as quickly as it came.

“I’m gonna… kill him.” Jimbo said angrily gritting his teeth.

“Uh, you gonna go in there while they’re-“

“No! But I’m gonna be here when they fucken come out of there.” Jimbo said as he plopped down in a chair across the room from Kearney. He just sat there, continuing to grit his teeth in anger.

…

“Lisa, I gotta stop I’m…” Dolph moaned slightly, but she pulled him closer to her. She kissed him passionately and he released into her. He moaned into her mouth and she felt his hot breath against her mouth.

“L-Lisa I-I… love you…!” He gasped.

She smiled and kissed him sweetly this time.

“W-we didn’t use…”

“It’s fine, I’m on birth control. Relax.” Lisa whispered to him. She felt him relax on top of her, his tension disappearing.

            This didn’t stop Lisa from having a mental headache. She couldn’t believe that she did this, or at least _now_. What about Jimbo? A part of her loved being with Dolph, but the other part wanted to disappear. She supposed she would have to talk to Jimbo about it… talk to both of them about… this situation. Lisa winced. She didn’t want to tell Jimbo that she just now decided to sleep with his best friend because she just now just realized Dolph had feelings for her, and that Dolph wasn’t actually ignoring her. Lisa didn’t want to believe that she only used Jimbo as a replacement, or did she? What she also felt for Jimbo was genuine even if… what if she has to choose? Who should she choose? Could she?

            Dolph slid next her and kissed her again, noticing that she looked as if she had something her mind. He thought he knew what, but he didn’t want to push her right now. After this she had to choose him, right? Jimbo was just a mistake, right? _Right?_

…

            Jimbo was still in Dolph and Kearney’s living room,  quietly scowling to himself. Kearney would nervously glance over at him once in a while, trying to make idle conversation, but Jimbo never replied.

“I love you Lisa. Yeah, I’ll show you something to love with my fucking fist in your face you scuz.” Jimbo thought that Dolph must’ve manipulated her somehow. Dolph was the type of guy to do that, and he wouldn’t be surprised one bit if she didn’t actually want to be in this situation, or if Dolph was just lying to her to get her to sleep with him…

            Dolph and Lisa both eventually sauntered out of the bedroom, and into the living room, both having slight bedhead from their…escapade. Dolph didn’t even have time to assess the situation he was in before he was aggressively pinned against a wall by, surprise, surprise, his best friend Jimbo. Lisa gasped and couldn’t speak due to her shock. She took a few steps back from the two, watching in horror. Kearney jolted up, watching the scenario happening in front of him.  

            “What the fuck?!-Gah!” Dolph had the wind blown out of him by a swift and hard punch to the stomach followed by another to his face. Dolph was a bit dazed, but he knew that the sock to the face was going to leave him with a black eye. He glared back at his enraged friend.

“What the fuck’s your problem?!” Dolph snapped angrily at Jimbo. Infuriated, Jimbo replied,

“My problem? What the fuck’s yours? What do you think you’re doing with her you fucking…!” Jimbo couldn’t even finish his sentence he was seething with so much anger, and decided to just punch him in the stomach again, making him gasp for air.  

            Lisa continued to subconsciously back up to the front door of the apartment that lead to her exit. She was watching the two, tears starting flowing from her eyes.

“Uh, guys, maybe you can just talk it out, I think you’re scaring the lady-“ Kearney tried to say, but was cut off.

“ _Shut the fuck up.”_ Jimbo snapped at Kearney. Dolph tried to get up, but had difficulty doing so. Jimbo turned and faced Lisa.

“What did he do to you? What did he make you do?” Jimbo demanded bitterly.

            Lisa could only continue to slowly back up toward the door, whimpering with tears in her eyes.

“I didn’t make her do anything she didn’t wanna do.” Dolph growled at Jimbo, he continued to hold his stomach as he got up.  

            Jimbo slammed him back against the wall at this response.

“Yeah, like I’m gonna believe you-“ Jimbo started

“He’s n-not lying.” Lisa stammered through her tears. She could hardly stand to look at either of them, but she couldn’t bear to see him hurt Dolph anymore, either.

            Jimbo’s grip tightened on Dolph’s shirt, but his attention was averted over to Lisa, who had completely backed herself up against the front door.

“What?! Why?! Why would you…?” Jimbo protested.

            Lisa still couldn’t say anything, just cry.

“Did none of it mean anything to you?!” Jimbo demanded.

            Lisa still didn’t’ respond, she just looked to the side, whimpering and shaking like a scared dog. Those words echoed in her mind before she snapped and ran out the door. She just continued to run. She didn’t look back and decided to make her way back home.

            “Yeah, hard to take it when it’s happening to you, huh?” Dolph slurred, but he still managed to let out a sly smile.

            Jimbo scowled back at Dolph, dropped him, then instinctively started to head after her, but was stopped by Kearney, who just shook his head as to say ‘not a chance in hell’. Kearney then stopped Dolph who, in a half daze also tried to get up and leave after her after being let from the grasp of his now enemy.  

            “The last thing you two need to do is run after her. Fucken work things out first.” Kearney said at the two, very annoyed at the whole situation. The two scowled at Kearney before sighing in defeat.

**Notes for the Chapter:**

> Aren't feuds just so fun to write? Ha   
> I'm totally not a Jimsa or Dolsa addict or anything. *lying*


	5. I Hate You

 

            “What the fuck is wrong with you?!” Dolph shouted at Jimbo from across the room.

            “Me?! What the fuck is wrong with you?! You fucking slept with my girlfriend-“

            “Tch, girlfriend? That isn’t what she said.” Dolph smirked.

            Jimbo started to approach Dolph, ready to try and beat him up some more, but Kearney stopped him from doing so.  

“Hey, guys. Cool it! Obviously there’s just a misunderstanding and-“ Kearney tried explaining, but was interrupted by Jimbo.

“Yeah, that’s right. And when it’s over I’m gonna make sure this guy disappears for a long time.“ Jimbo growled, trying to get passed Kearney and toward Dolph. Dolph continued to give Jimbo that sly smirk that put him over the edge.

“You’re the one who’s gonna disappear. She made a mistake because you just happened to be there at the right place and time to take advantage of her!” Dolph argued.

“You fucken liar! You’re the mistake. You were just pretending to be friends with her just so you could fuck her!” Jimbo snapped back. Dolph’s smirk quickly turned into a scowl.

“Guys!” Kearney yelled, but the two continued to ignore him.

“You don’t even know her as well as I do, how can you honestly believe you’re not the mistake?” Dolph retorted.

“I know her better than you do.” Jimbo scowled back.

“That’s where you’re wrong, asshole.” Dolph smirked again.

            Although infuriated, Jimbo couldn’t disprove what Dolph had said. Jimbo confirmed this with Lisa, but that didn’t change the fact that he could’ve easily manipulated her. Jimbo replied angrily,

“Yeah, I’m sure that’s how you were able to get her to sleep with you. I bet you told her a bunch of lies like you tell all those other girls. That’s the only way you get any-“

“Like you’re the one to talk!” Dolph snapped. “I bet you can’t wait to add another virgin notch to your belt that you can brag about huh?! Lisa’s different, and not just another prize you can claim after fucking it!” Dolph yelled, trying to lunge at Jimbo, but was kept at bay by Kearney.

            Although Kearney was a large guy, he was struggling to keep the two from killing each other right here and now in the living room. He’d never seen the two argue over something so intensely before.

“Come on you two, make a deal or something. Can’t you two just share her or something once in a while?” Kearney said exasperated. The two glared at him furiously.

 “Fuck no!” Jimbo scowled.  Dolph gave Kearney a sour look that said the same.

“Oh come on, you two have banged the same chick before. I mean, I think all three of us have been with Shauna-”

 _“I love Lisa!”_ The two yelled at Kearney simultaneously, looked back at each other hesitantly before switching back to glares of rage.

“Uhhh…” Kearney looked over at one and then the other, worried. This wasn’t really going anywhere. Also, he was wondering about both of their sanities at this point. They both were claiming their love for Lisa Simpson of all people, which, no matter how much either claimed they knew her, he didn’t think that either of them really did know a whole lot about her. That outburst must’ve calmed the two down enough since they both sat back down, but both of them were still shooting venomous glares at each other.  

“I’m leaving.” Jimbo finally announced.

“You better not be going after her.” Dolph warned.  

“Neither of you are going after her.” Kearney said annoyed. “You both need to chill or something.”

“Fine, I won’t go after her, but if I find out you did, you’re dead.” Jimbo threatened.

“Whatever, fine.” Dolph said in reply.

Jimbo left and Kearney sighed, lying down into the couch.

 _“Finally.”_ Kearney mumbled.

**Notes for the Chapter:**

> I honestly have no idea where I'm gonna go with this. Haha.


	6. Blues

Lisa ran up to her room crying. The only one who paid any attention to her was Bart. “Oh, she’s just going through some normal ol’ teenage crisis that all girls her age go through.” Homer said, not at all worried. “Are you sure Homie? Well, let’s see if she’s better when she comes back down.” Marge added with slight concern. Bart was a little more worried though since the last time he saw her she was with his on-again-off-again-friend-slash-bully-slash-arch-nemesis-slash-partner-in-crime James “Jimbo” Jones. “He better not have done anything to hurt Lis’.” Bart thought angrily. He decided to run up the stairs after Lisa and see what she was crying about. He entered her room unannounced like he always had in their younger years, both of them were pretty used to it. Right away he saw her crying into the pillow of her old bed she hadn’t slept in since her last vacation from college. “Lis’!? What’s wrong? Did Jimbo do something to hurt you?! I told you he was a scumbag!” Bart exclaimed. Lisa looked up at him before starting to cry again. Through tears she forced herself to talk. “N-no, he didn’t do anything… i-it’s what I-I did…” Lisa stammered. “C’mon Lis’, I know you’re hard on yourself, but come on. I doubt anything that happened was your fault and not his-!” “I slept with Dolph!” Lisa wailed and stuffed her face back into her pillow. “Uh…oh. Eugh.” Bart gagged before recomposing herself. He didn’t want to think of his sister doing any of those things with anyone especially with either Jimbo or Dolph. Bart reluctantly patted her shoulder, but didn’t know what to say that would console her in any way. He quietly backed out of the room, shut the door, and backed down the stairs. “Bart, do you know what your sister is crying about?” Marge asked fro

Lisa ran up to her room crying. The only one who paid any attention to her was Bart.

“Oh, she’s just going through some normal ol’ teenage crisis that all girls her age go through.” Homer said, not at all worried.  

“Are you sure Homie? Well, let’s see if she’s better when she comes back down.” Marge added with slight concern.

            Bart was a little more worried though since the last time he saw her she was with his on-again-off-again-friend-slash-bully-slash-arch-nemesis-slash-partner-in-crime James “Jimbo” Jones.

            _“He better not have done anything to hurt Lis’.”_ Bart thought angrily. He decided to run up the stairs after Lisa and see what she was crying about. He entered her room unannounced like he always had in their younger years, both of them were pretty used to it. Right away he saw her crying into the pillow of her old bed she hadn’t slept in since her last vacation from college.

“Lis’!? What’s wrong? Did Jimbo do something to hurt you?! I told you he was a scumbag!” Bart exclaimed.

            Lisa looked up at him before starting to cry again. Through tears she forced herself to talk.

“N-no, he didn’t do anything… i-it’s what I-I did…” Lisa stammered.

“C’mon Lis’, I know you’re hard on yourself, but come on. I doubt anything that happened was your fault and not his-!”

“I slept with Dolph!” Lisa wailed and stuffed her face back into her pillow.

“Uh…oh. Eugh.” Bart gagged before recomposing herself. He didn’t want to think of his sister doing any of those things with anyone especially with either Jimbo or Dolph.

            Bart reluctantly patted her shoulder, but didn’t know what to say that would console her in any way. He quietly backed out of the room, shut the door, and backed down the stairs.

“Bart, do you know what your sister is crying about?” Marge asked from the kitchen looking concerned.

“Uh, just boy problems.” Bart said awkwardly.

“See, honey, like I said. Teen girl problems.” Homer chuckled.

…

            Lisa fell asleep crying, and when she woke up she regretfully looked at her phone. She felt sick again. Her phone was blown up with messages from both Jimbo and Dolph… and even a few from Milhouse, but they were nearly drowned out in between the masses of pleading calls and texts. Lisa groaned and buried her head back into her pillow before eventually waking herself completely up.

            Lisa went downstairs where her mother was already awake and cooking breakfast in her sing-song cheery demeanor. She was joined by a 10, going on 11 year old Maggie waiting for her school bus. Her father and brother were still asleep in bed.

“Hey, sweetie? Are you feeling okay? I know breakups can be hard.” Marge said, trying to be understanding toward her daughter. Lisa looked back at her confused.

“What? I’m not going through a breakup…” Lisa mumbled. She wondered if that would be easier than what she was going through.

“Oh, Bart said you were having boy troubles so I just thought…” Marge said slightly confused.

“That someone is breaking up with me, huh?” Lisa replied annoyed.

“Well…” Marge mumbled.

“Actually, that’s not the problem at all. There are two people who like me a lot and I’m not sure who I should choose…” Lisa said as a matter of fact, but still slightly annoyed at her mother’s assuming nature.

“Well, you never know. Neither could be the right answer.” Marge said smiling, still trying to be helpful, and sing-songy, but to Lisa it felt futile.

            Lisa sighed and looked into her cereal drenched in soymilk. She didn’t feel like eating.   


“So who are these lucky two boys? Anybody we know in Springfield?” Marge asked curiously. Maggie was secretly eavesdropping in the background, she was also curious to hear, especially if it was any of the deadbeats in Springfield.

“Oh-oh, wait let me guess. Milhouse and… Nelson?” Marge asked, trying to sound sly.

“Ugh, mom, _no_.” Lisa grimaced. “Though, they are from Springfield…” Lisa mumbled, not sure if she wanted to reveal who either were, since she knew their reputations weren’t that great in Springfield… they’ve calmed down with age, but she thought that didn’t really change how some people thought of them.

“Well, I’m stumped, then. I have no idea who it could be.” Marge said, giving up easily.

            Lisa gave her mom a flat yet still annoyed look. _She really couldn’t think of anyone who could possibly ever like her. Typical family._ She thought and sighed.

“James Jones, and Dolph Starbeam.” Lisa grumbled annoyed. Just then Bart meandered tiredly into the room. Maggie was silently giggling in the background.

“Oh, those names sound familiar…! Oh, one used to watch you guys when you were little, and the other… didn’t he steal your dolls once? Also, aren’t they Bart’s friends?” Marge asked curiously, a bit hazy on the subject. Lisa burned bright red, she forgot about her dolls. She later heard that Jimbo stole them because he thought they were demeaning to women… and she actually felt touched by that.

“Uh, wha, huh?” Bart said tiredly. He was so tired that he didn’t realize that when he sat down he started eating out of Lisa’s untouched cereal bowl.

“Well, if they’re friends with my little man, then I’m sure they’re fine.”

“Mom, I’m 20.” Bart said unamused. Marge giggled her shrill laugh in response.

            Lisa sighed and got up. She decided she would go on a walk to get some fresh air. Home wasn’t helping her much.

“Be safe outside, sweetie!” Marge called out.  

m the kitchen looking concerned. “Uh, just boy problems.” Bart said awkwardly. “See, honey, like I said. Teen girl problems.” Homer chuckled. … Lisa fell asleep crying, and when she woke up she regretfully looked at her phone. She felt sick again. Her phone was blown up with messages from both Jimbo and Dolph… and even a few from Milhouse, but they were nearly drowned out in between the masses of pleading calls and texts. Lisa groaned and buried her head back into her pillow before eventually waking herself completely up. Lisa went downstairs where her mother was already awake and cooking breakfast in her sing-song cheery demeanor. She was joined by a 10, going on 11 year old Maggie waiting for her school bus. Her father and brother were still asleep in bed. “Hey, sweetie? Are you feeling okay? I know breakups can be hard.” Marge said, trying to be understanding toward her daughter. Lisa looked back at her confused. “What? I’m not going through a breakup…” Lisa mumbled. She wondered if that would be easier than what she was going through. “Oh, Bart said you were having boy troubles so I just thought…” Marge said slightly confused. “That someone is breaking up with me, huh?” Lisa replied annoyed. “Well…” Marge mumbled. “Actually, that’s not the problem at all. There are two people who like me a lot and I’m not sure who I should choose…” Lisa said as a matter of fact, but still slightly annoyed at her mother’s assuming nature. “Well, you never know. Neither could be the right answer.” Marge said smiling, still trying to be helpful, and sing-songy, but to Lisa it felt futile. Lisa sighed and looked into her cereal drenched in soymilk. She didn’t feel like eating. “So who are these lucky two boys? Anybody we know in Springfield?” Marge asked curiously. Maggie was secretly eavesdropping in the background, she was also curious to hear, especially if it was any of the deadbeats in Springfield. “Oh-oh, wait let me guess. Milhouse and… Nelson?” Marge asked, trying to sound sly. “Ugh, mom, no.” Lisa grimaced. “Though, they are from Springfield…” Lisa mumbled, not sure if she wanted to reveal who either were, since she knew their reputations weren’t that great in Springfield… they’ve calmed down with age, but she thought that didn’t really change how some people thought of them. “Well, I’m stumped, then. I have no idea who it could be.” Marge said, giving up easily. Lisa gave her mom a flat yet still annoyed look. She really couldn’t think of anyone who could possibly ever like her. Typical family. She thought and sighed. “James Jones, and Dolph Starbeam.” Lisa grumbled annoyed. Just then Bart meandered tiredly into the room. Maggie was silently giggling in the background. “Oh, those names sound familiar…! Oh, one used to watch you guys when you were little, and the other… didn’t he steal your dolls once? Also, aren’t they Bart’s friends?” Marge asked curiously, a bit hazy on the subject. Lisa burned bright red, she forgot about her dolls. She later heard that Jimbo stole them because he thought they were demeaning to women… and she actually felt touched by that. “Uh, wha, huh?” Bart said tiredly. He was so tired that he didn’t realize that when he sat down he started eating out of Lisa’s untouched cereal bowl. “Well, if they’re friends with my little man, then I’m sure they’re fine.” “Mom, I’m 20.” Bart said unamused. Marge giggled her shrill laugh in response. Lisa sighed and got up. She decided she would go on a walk to get some fresh air. Home wasn’t helping her much. “Be safe outside, sweetie!” Marge called out.


	7. Making It Up

Lisa decided that she would go on a walk in the park. She needed to clear her mind. She found a vacant park bench to sit on while she scrolled through her phone. She wasn’t sure who she would respond to first. She thought maybe she should talk to Jimbo first since he was, to her surprise, extremely upset by the whole ordeal. A big part of her thought that she was just a temporary thing for him… but that little episode the previous day had changed everything.

            “Well, look who it is.” Jimbo said playfully as he snuck up from behind her. He put his arms around her gently on her shoulders from behind. That didn’t stop her from being absolutely terrified. She remembered what he did to Dolph and a part of her wondered if she would be next after trying to explain to him the events that lead to yesterday’s encounter. Jimbo felt her tense up and backed off of her instantly. He cautiously sat next to her on the bench.

“I didn’t mean to scare you.” He said, slightly worried. He could tell she was afraid of him. Likely from what happened yesterday.

“I-I…” She tried to speak, but the words wouldn’t come out. She looked terrified and it made him sad. He gently put his hand on hers.

“Lisa… you know I’d never hurt you right?”

            Lisa slowly started to calm down.

            _Do I know that? Do I really know him all that well? It’s been years. Do we really know anyone?_ Thoughts were racing around in her head, even ones that didn’t make sense. However, Lisa decided that his words seemed genuine enough, so she decided there shouldn’t be anything to worry about.

“I-I’m sorry…” She whispered, barely audible enough for him to hear.

            Jimbo smiled at her, but it was a sad one. He slightly squeezed her hand. Lisa couldn’t take the guilt any longer. She started to cry and buried herself in his chest. Jimbo was shocked momentarily, but quickly started to comfort her.

“I-I didn’t mean to make you upset… I-I thought you… I thought you didn’t want…” Lisa choked a bit and continued to cry.

“Lisa, don’t say that!… I thought you were my girlfriend. Well, I want you to be…” Jimbo turned red in embarrassment. Lisa continued to cry.

“Y-you’ll never want me now…” She stammered.

“What? Of course I do.” He said disbelievingly before holding her tight. Lisa stopped shaking. When his hold on her loosened up she looked up at him. He kissed her and she returned it passionately. She buried her head into his chest and he continued to comfort her. They stayed that way for a while until she was able to calm completely down.

…

“I’ll give you some space… maybe we could see each other tomorrow?” Jimbo asked Lisa hopefully.

“Okay, I would like that…” She smiled, wiping away the tears from her eyes. She continued to sit on the bench as she watched him walk off. Even when he was gone she looked down the path dreamily. 10 years ago if anyone told her she would be Jimbo Jones’ girlfriend she would’ve busted out laughing in disbelief.

 “So, was it all in my head?”

Lisa turned around to see Dolph leaning against one of the lampposts.

“I guess it was all just some elaborate dream.” He sighed. She stared at him. She couldn’t cry anymore, her eyes were wide, but dry. She didn’t quite know how to react.

“Do you remember what you said?”

            Lisa tried to speak, but nothing would come out again, she reverted back to her mute state.

 _“I-I wish…”_ She mouthed, but she couldn’t say the words.

“’If I were older, I’d choose you.’ That’s what you said when I said you were too young. Tell me you remember…” Dolph said sadly.

“I wish I were older…” Lisa murmured quietly and looked down.

“Tell me I’m wrong, and I’ll leave you alone.” He said, looking at her with such hurt in his eyes, it made her knees weak.

            Lisa quickly had to sit back down on the bench, her legs were going to collapse from her nervousness.  

“Was it a lie, or am I making it up?” Dolph asked again, but this time he stood in front of her.  Lisa ended up passing out.  

…

**Author's Note:**

> Author’s note: If you couldn’t tell by now… I really like Jimbo and Lisa together. Bahaha. I know I haven’t finished An Unhealthy Obsession… But I’ve actually written most of it, and I’m just very bad and slow at editing. I also wanted to work on something not as long, and was more of a one-shot. I think I’m going to add more to this story eventually.


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